1,5-Diaminonaphthalene
Chemical compound
From Wikipedia, the free encyclopedia
1,5-Diaminonaphthalene is an organic compound with the formula C10H6(NH2)2. It is one of several diaminonaphthalenes. It is a colorless solid that darkens in air due to oxidation.
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| Names | |
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| Preferred IUPAC name
Naphthalene-1,5-diamine | |
| Other names
Alphamin, 1,5-DAN | |
| Identifiers | |
3D model (JSmol) |
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| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| ECHA InfoCard | 100.017.108 |
| EC Number |
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| KEGG | |
PubChem CID |
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| RTECS number |
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| UNII | |
| UN number | 3077 |
CompTox Dashboard (EPA) |
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| Properties | |
| C10H10N2 | |
| Molar mass | 158.204 g·molâ1 |
| Appearance | white solid |
| Density | 1.4 |
| Melting point | 185â187 °C (365â369 °F; 458â460 K) |
| Structure[1] | |
| monoclinic | |
| P21/c | |
a = 5.1790, b = 11.008, c = 21.238 | |
Lattice volume (V) |
1210.7 |
Formula units (Z) |
6 |
| Hazards | |
| GHS labelling: | |
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| Warning | |
| H351, H410 | |
| P201, P202, P273, P281, P308+P313, P391, P405, P501 | |
| Flash point | 226 °C (439 °F; 499 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis and reactions
It is prepared by reduction of 1,5-dinitronaphthalene, which in turn is obtained with the 1,8-isomers by nitration of 1-nitronaphthalene. It can also be prepared by treatment of 1,5-dihydroxynaphthalene with ammonium sulfite. It is a precursor to naphthalene-1,5-diisocyanate, a precursor to specialty polyurethanes.[3]
1,5-Diaminonaphthalene is a precursor imine-linked covalent organic frameworks.[4]
Applications
Analytical matrix for MALDI/LDI. 1,5-Diaminonaphthalene (often as the hydrochloride salt) is used as a low-background matrix for MALDI mass spectrometry, including mass spectrometry imaging (MSI) of small molecules in tissue sections.[5] It has also been reported as a highly performing electron-transfer matrix for LDI analyses of low-mass species.[6]
Precursor to naphthalene-1,5-diisocyanate (NDI). 1,5-Diaminonaphthalene is an industrial intermediate to diisocyanates, notably naphthalene-1,5-diisocyanate (NDI), which is used to make high-performance polyurethane elastomers (marketed as Vulkollan, based on Desmodur 15).[7][8]